1-Piperazinecarboxylic acid, ethyl ester → HCID 66920071, compound

HRID 1908618Notes

Reaction equation

HRID 1908618 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH2:14][S:15]([CH3:18])(=[O:17])=[O:16])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.[CH2:41]([O:43][C:44]([N:46]1[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]1)=[O:45])[CH3:42]>CN(C=O)C.C(=O)([O-])O.[Na+]>[CH2:41]([O:43][C:44]([N:46]1[CH2:47][CH2:48][N:49]([C:10](=[O:12])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:14][S:15]([CH3:18])(=[O:17])=[O:16])[CH2:50][CH2:51]1)=[O:45])[CH3:42]

Participants

6

Reactant 3

HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 7017894Boc-Met(O2)-OH

Product 1

HCID 66920071HCID 66920071, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 2 g of (S)-2-tert-Butoxycarbonylamino-4-methanesulfonyl-butyric acid, 3.2 g of NEM and 2.3 g of TOTU in 10 ml of DMF, 1.2 g of piperazine-1-carboxylic acid ethyl ester was added at RT and stirred for 2 h. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution and extracted with 400 ml of ethyl acetate. The organic phase was washed with diluted saturated aqueous sodium hydrogen carbonate solution and dried over MgSO4 and the solvents were removed under reduced pressure. The crude product was purified by chromatography on silica gel eluting with a gradient of n-heptane/ethyl acetate. The fractions containing the product were combined and the solvent evaporated under reduced pressure.

Workup

  1. extractionextracted with 400 ml of ethyl acetate
  2. washThe organic phase was washed with diluted saturated aqueous sodium hydrogen carbonate solution
  3. dry with materialdried over MgSO4
  4. customthe solvents were removed under reduced pressure
  5. customThe crude product was purified by chromatography on silica gel eluting with a gradient of n-heptane/ethyl acetate
  6. additionThe fractions containing the product
  7. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-5fdf81168e6c40539ef286bec518a17c
Source dataset
uspto-grants-2013_12
Patent number
US08598179B2

Reaction notes

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